Operation Pickering 1940s Weekend: Your Base Is Confirmed
Transmission begins.
Orders are now confirmed. The Pickering 1940s Weekend will take place from 9 to 11 October 2026, bringing one of North Yorkshire’s most immersive heritage events back to the town of Pickering.
If you are planning to attend the Pickering 1940s Weekend, Cliff House Holiday Cottages offers a well-positioned and practical base. Located just 15 minutes from Pickering by car, or accessible via a short bus journey, our cottages allow visitors to stay close to the event while returning to space, comfort, and countryside at the end of each day.
Staying near the Pickering 1940s Weekend
The Pickering 1940s Weekend is known for its attention to detail. Expect military vehicles, re-enactors, period music, shopfronts dressed for the era, and a town fully committed to stepping back in time. Some visitors arrive in full uniform or vintage dress, others prefer to attend as observers, photographers, or history enthusiasts.
Cliff House Holiday Cottages works well for all of these approaches. Guests can head into Pickering early, spend the day immersed in the event, then return to open fires, generous living spaces, and the freedom of two acres of gardens and woodland.
Combine the Pickering 1940s Weekend with Eden Camp
Many visitors choose to extend their Pickering 1940s Weekend by visiting Eden Camp Modern History Museum, located a short drive from Cliff House. Set on the site of a former prisoner-of-war camp, Eden Camp provides powerful context to the wartime period and complements the Pickering event particularly well.
Staying at Cliff House makes it easy to combine both experiences without long journeys or packed itineraries.
A practical base for October 2026
October is a strong time to explore North Yorkshire. Days are often clear, the Moors take on autumn colour, and evenings lend themselves to fires, shared meals, and time together. For groups attending the Pickering 1940s Weekend, our multiple cottages allow people to stay close while retaining their own space.
Accommodation for the Pickering 1940s Weekend traditionally fills early.
If October 2026 is already in your sights, securing your base sooner rather than later is advised.
